Ascaroside and plant nutrient combinations and methods for use

Abstract

Combinations of agents for enhancing plant growth and methods of their use are provided. The combinations comprise at least one ascaroside (or a derivative or analog of an ascaroside) with at least one plant nutrient. The ascaroside(s) and plant nutrient(s) may be provided in the same composition or may be applied together (e.g., substantially simultaneously) or sequentially.

Description

[0001] ASCAROSIDE AND PLANT NUTRIENT COMBINATIONS AND METHODS FOR USE CROSS-REFERENCE TO RELATED APPLICATIONS [1] This application claims the benefit of priority to U.S. Provisional Appl. No. 63 / 515,554, filed July 25, 2023, the entirety of which is hereby incorporated by reference. FIELD OF THE INVENTION [2] The invention is drawn to compositions and methods relating to use of an ascaroside and one or more plant nutrients. BACKGROUND OF THE INVENTION [3] Plant nutrients are important to the growth and development of plants as well as to the production and quality of their flowers and fruits. Plant nutrients are also required to allow plants to produce chlorophyll and carry out photosynthesis. [4] A number of essential and beneficial plant nutrients have been recognized, each serving an important function in promoting the growth and development of plants, flowers, and fruits. One or more (and typically more than one) plant nutrient is typically applied to any given crop- producing plant (“crop”) over the course of its growth. To effectively address plant nutrient deficiencies as well as prevent pathogen damage over the life of a plant, separate applications of these components are generally required. This is detrimental because it requires additional passes over the crop which increases costs, resource use (e.g. fuel, water, labor, etc), and potential damage to the crop and / or soil. SUMMARY OF THE INVENTION [5] Combinations of agents for promoting plant growth and methods of their use are provided. The combinations comprise at least one ascaroside (or a derivative or analog of an ascaroside) with at least one plant nutrient. The ascaroside can be combined with at least one plant nutrient to provide the plant with components needed for its growth while also providing for long-lasting protection against pathogens (e.g. fungi, molds, bacteria, viruses, and / or nematodes) during the life of the plant. The ascaroside(s) and nutrient(s) may be provided in the 1 409753-015WO (210651) BUSINESS.31699770.1 same composition or may be applied together (i.e., substantially simultaneously) or sequentially. The agents are applied in an effective amount, i.e., an amount sufficient to provide the plant with nutrient(s) to enhance growth and development and also to provide long-lasting protection against pathogens. [6] The invention includes, without limitation, the following embodiments. [7] Embodiment 1: A method for providing nutrients and protection against pathogens to a plant, comprising contacting a plant, a plant part, or soil surrounding a plant with an effective amount of a combination of agents, said agents comprising one or more ascaroside and one or more plant nutrients. [8] Embodiment 2: The method of Embodiment 1, wherein the one or more plant nutrients comprise one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof. [9] Embodiment 3: The method of Embodiment 1 or 2, wherein the macronutrients are selected from nitrogen-containing nutrients, phosphorus-containing nutrients, potassium- containing nutrients, and combinations thereof.

[0010] Embodiment 4: The method of any one of Embodiments 1-3, wherein the one or more plant nutrients are in the form of a mixture of nitrogen-containing nutrients, phosphorus- containing nutrients, and potassium-containing nutrients.

[0011] Embodiment 5: The method of Embodiment 2, wherein the macronutrients are selected from calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0012] Embodiment 6: The method of any one of Embodiments 1-5, wherein the one or more plant nutrients are in the form of manure / guano, fish emulsion, bone meal, blood meal, biofertilizers, or cover crops.

[0013] Embodiment 7: The method of any one of Embodiments 1-6, wherein the one or more plant nutrients comprise one or more micronutrients selected from the group consisting of boron- containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof. 2 409753-015WO (210651) BUSINESS.31699770.1

[0014] Embodiment 8: The method of any one of Embodiments 1-7, wherein the one or more plant nutrients comprise one or more macronutrients and one or more micronutrients.

[0015] Embodiment 9: The method of any one of Embodiments 1-8, wherein the one or more ascarosides comprises an ascaroside having the structure (I): OZ , where Z is an optionally substituted C3-40aliphatic group, and each of -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g. -a moiety -C(O)ORc), a C2-20 carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20 thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0016] Embodiment 10: The method of Embodiment 9, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group, ii. – CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally 3 409753-015WO (210651) BUSINESS.31699770.1 substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)– (CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0017] Embodiment 11: The method of Embodiment 9, wherein Z is selected from the group consisting of: x. –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n– CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an 4 409753-015WO (210651) BUSINESS.31699770.1 optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or xvii. –(CH2)n–C(O)– CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0018] Embodiment 12: The method of any one of Embodiments 9-11, wherein Raand Rbare each -H.

[0019] Embodiment 13: The method of any one of Embodiments 9-12, wherein Z is –CH(CH3)– (CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0020] Embodiment 14: The method of any one of Embodiments 1-13, wherein one or more ascarosides comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. 5 409753-015WO (210651) BUSINESS.31699770.1

[0021] Embodiment 15: The method of any one of Embodiments 1-13, wherein the one or more ascarosides comprises ascr#18.

[0022] Embodiment 16: The method of any one of Embodiments 1-15, wherein the one or more ascarosides and the one or more plant nutrients are applied simultaneously or substantially simultaneously.

[0023] Embodiment 17: The method of any one of Embodiments 1-16, wherein the one or more ascarosides and the one or more plant nutrients are contained within the same composition.

[0024] Embodiment 18: The method of any one of Embodiments 1-15, wherein the one or more ascarosides and the one or more plant nutrients are applied sequentially (in either order).

[0025] Embodiment 19: The method of any one of Embodiments 1-18, wherein the combination is used as a seed coating.

[0026] Embodiment 20: A composition comprising one or more ascarosides and one or more plant nutrients.

[0027] Embodiment 21: The composition of Embodiment 20, wherein the one or more ascarosides and the one or more plant nutrients are present in effective amounts.

[0028] Embodiment 22: The composition of Embodiment 20 or 21, wherein the one or more plant nutrients comprise one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

[0029] Embodiment 23: The composition of Embodiment 22, wherein the macronutrients are selected from nitrogen-containing nutrients, phosphorus-containing nutrients, potassium- containing nutrients, and combinations thereof.

[0030] Embodiment 24: The composition of any of Embodiments 20-23, wherein the one or more plant nutrients are in the form of a mixture of nitrogen-containing nutrients, phosphorus- containing nutrients, and potassium-containing nutrients.

[0031] Embodiment 25: The composition of Embodiment 22, wherein the macronutrients are selected from calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof. 6 409753-015WO (210651) BUSINESS.31699770.1

[0032] Embodiment 26: The composition of any of Embodiments 20-25, wherein the one or more plant nutrients are in the form of manure / guano, fish emulsion, bone meal, blood meal, biofertilizers, or cover crops.

[0033] Embodiment 27: The composition of any of Embodiments 20-26, wherein the one or more plant nutrients comprise one or more micronutrients selected from the group consisting of boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron- containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc- containing nutrients, and combinations thereof.

[0034] Embodiment 28: The composition of any of Embodiments 20-27, wherein the one or more plant nutrients comprise one or more macronutrients and one or more micronutrients.

[0035] Embodiment 29: The composition of any one of Embodiments 20-28, wherein the one or more ascarosides comprises an ascaroside having the structure (I): OZ , wherein Z is an optionally substituted C3-40 aliphatic group, and -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g. -a moiety -C(O)ORc), a C2-20 carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. 7 409753-015WO (210651) BUSINESS.31699770.1

[0036] Embodiment 30: The composition of Embodiment 29, wherein Z is selected from the group consisting of: i. –CH(CH3)–R1, where R1is an optionally substituted C1-40 aliphatic group; ii. –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iii. –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; iv. –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; v. –CH(CH3)–(CH2)n–C(O)–CH2- CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vi. –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; vii. –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; viii. –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and ix. –(CH2)n–C(O)– CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0037] Embodiment 31: The composition of Embodiment 29, wherein Z is: x. –CH(CH3)– (CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xi. –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted 8 409753-015WO (210651) BUSINESS.31699770.1 aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xii. –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiii. –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xiv. –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xv. –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; xvi. –(CH2)n– CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon- containing linker moiety to another ascaroside molecule; or xvii. –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. 9 409753-015WO (210651) BUSINESS.31699770.1

[0038] Embodiment 32: The composition of any one of Embodiments 29-31, wherein Raand Rbare each -H.

[0039] Embodiment 33: The composition of any one of Embodiments 29-32, wherein Z is – CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0040] Embodiment 34: The composition of any one of Embodiments 20-33, wherein the one or more ascarosides comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.

[0041] Embodiment 35: The composition of any one of Embodiments 20-33, wherein the one or more ascarosides comprises ascr#18.

[0042] Embodiment 36: The composition of any one of Embodiments 20-35, wherein said composition is in a liquid form.

[0043] Embodiment 37: The composition of Embodiment 36, wherein the liquid form is a sprayable formulation.

[0044] Embodiment 38: The composition of any one of Embodiments 20-35, wherein the composition is in a solid form.

[0045] Embodiment 39: The composition of Embodiment 38, wherein said solid form comprises powder or granules.

[0046] Embodiment 40: The composition of any one of Embodiments 20-39, wherein said composition is in liquid form.

[0047] Embodiment 41: The composition of any one of Embodiments 20-40, wherein the composition is stable for a period of greater than 6 months.

[0048] Embodiment 42: The composition of any one of Embodiments 20-41, wherein the composition further comprises one or more additional components selected from the group consisting of surfactants, including emulsifiers, dispersants, foam-formers, colorants, processing aids, lubricants, fillers, reinforcements, flame retardants, light stabilizers, ultraviolet radiation absorbers, weather stabilizers, plasticizers, release agents, perfumes, heat-retaining additives (e.g., silica), cross-linking agents, antioxidants, anti-foaming agents, buffers, pH modifiers, compatibility agents, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents. 10 409753-015WO (210651) BUSINESS.31699770.1

[0049] These and other features, aspects, and advantages of the disclosure will be apparent from a reading of the following detailed description together with the accompanying drawings, which are briefly described below. The invention includes any combination of two, three, four, or more of the above-noted embodiments as well as combinations of any two, three, four, or more features or elements set forth in this disclosure, regardless of whether such features or elements are expressly combined in a specific embodiment description herein. This disclosure is intended to be read holistically such that any separable features or elements of the disclosed invention, in any of its various aspects and embodiments, should be viewed as intended to be combinable unless the context clearly dictates otherwise. DETAILED DESCRIPTION OF THE INVENTION

[0050] The disclosure provides compositions and methods relating to use of one or more ascarosides and one or more plant nutrients. As used herein, the term “ascaroside” includes the ascaroside, a derivative, an analog of the ascaroside, or combinations thereof, as will be described in further detail herein. The ascaroside can be used with any plant nutrient, as will also be descried in further detail herein.

[0051] The ascaroside(s) and the nutrient(s) may be used in the same composition, or the ascaroside(s) and the nutrient(s) may be applied separately (e.g., in separate formulations), either simultaneously or sequentially. If applied sequentially, the applications are close enough in time such that they are able to work in combination to produce the beneficial results.

[0052] As noted, methods and compositions of the invention comprise ascarosides. Ascarosides are secondary metabolites produced by nematodes. Many structurally diverse ascarosides have been identified in nature and are believed to function as an evolutionarily conserved chemical language used by nematodes to control many aspects of their development.

[0053] Ascarosides are derivatives of the sugar ascarylose—a di-deoxy sugar lacking hydroxyl groups at its 3- and 6-positions. Ascarosides have the general structure shown in Formula I: 11 409753-015WO (210651) BUSINESS.31699770.1 OZ I), wherein: Z is an optionally substituted C2-40 aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, where each Rcis independently at each occurrence selected from -H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

[0054] In certain embodiments, Z is: (i) –CH(CH3)–R1, where R1is an optionally substituted C1-40 aliphatic group (ii) –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a 12 409753-015WO (210651) BUSINESS.31699770.1 linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iii) –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (iv) –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (v) –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is - H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (vi) –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (vii) –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a 13 409753-015WO (210651) BUSINESS.31699770.1 linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (viii) –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (ix) –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0055] In certain embodiments, Z is: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a 14 409753-015WO (210651) BUSINESS.31699770.1 peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a 15 409753-015WO (210651) BUSINESS.31699770.1 nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; or (xviii) an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

[0056] As defined above and described herein, in some embodiments, Z comprises a nitrogen-, oxygen-, or sulfur-containing functional group. It will be appreciated that “an oxygen-containing functional group” refers to moieties that comprise one or more oxygen atoms (e.g., carbonyl- containing groups such as esters, aldehydes, carboxylic acids, ortho esters, and ketones; ethers, hydroxyls, and heterocyclic rings comprising one or more oxygen atoms and / or one of the foregoing functional groups); “a nitrogen-containing functional group” refers to moieties that comprise one or more nitrogen atoms (e.g., amines, amides, carbamates, imines, ureas, oximes, amidines, guanidines, nitriles, azo groups, azides, and heterocyclic rings comprising one or more nitrogen atoms and / or one of the foregoing functional groups); and “a sulfur-containing functional group” refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide).

[0057] In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising an oxygen-containing functional group. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a carboxylic acid. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising an aldehyde. In certain embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising an ester. In some embodiments, Z an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CO2R2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CO2H. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CO2CH3. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -CON(R3)2. In some embodiments, Z is an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising -N(R3)2. In some embodiments, Z is an optionally unsaturated, optionally 16 409753-015WO (210651) BUSINESS.31699770.1 substituted C2-40sidechain terminating in a chain end comprising an ester comprising a linker moiety covalently attached to one or more additional ascaroside molecules.

[0058] As described above, the ascarylose sugar moiety in the provided compounds can be substituted or unsubstituted (i.e., there can be functional groups other than -OH at 2- and 4- positions of the sugar or, stated differently, variables Raand / or Rbcan be other than -H in any of the formulae herein).

[0059] As defined above and described herein, each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1- 20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group, a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g., -a moiety -C(O)ORc), a C2-20carbamate (e.g., -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to an ascaroside molecule.

[0060] In certain embodiments, Rais -H. In certain embodiments, Rbis -H. In certain embodiments, Raand Rbare the same. In certain embodiments Raand Rbare both -H. In certain embodiments, Raand Rbare different. In certain embodiments, Rais -H, and Rbis other than -H. In certain embodiments, Rais other than -H and Rbis -H. In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)-2-methyl-2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2-hydroxy-2-(4-hydroxyphenyl)ethyl)amino)-4- oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4-hydroxyphenethyl)amino)-4- oxobutanoate. In certain embodiments, Racomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Rbcomprises a glycoside, amino acid, a peptide, or nucleotide. In certain embodiments, Racomprises a linkage to a second ascaroside molecule. In certain embodiments, Rbcomprises a linkage to an ascaroside molecule. In certain embodiments, Racomprises a sugar. In certain embodiments, Rbcomprises a sugar. 17 409753-015WO (210651) BUSINESS.31699770.1

[0061] In some embodiments, Rais an optionally substituted C1-20aliphatic. In some embodiments, Rais an optionally substituted C1-6 aliphatic. In some embodiments, Rais C1-20 aliphatic. In some embodiments, Rais C1-6 aliphatic. In some embodiments, Rais methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rais C1-20acyl. In some embodiments, Rais -C(O)Rc. In some embodiments, Rais -C(O)H. In some embodiments, Rais -C(O)CH3. In some embodiments, Rais an optionally substituted C1-20 heteroaliphatic. In some embodiments, Rais an optionally substituted C1-6heteroaliphatic. In some embodiments, Rais C1-20 heteroaliphatic. In some embodiments, Rais C1-6 heteroaliphatic. In some embodiments, Rais an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais optionally substituted aryl. In some embodiments, Rais optionally substituted phenyl. In some embodiments, Rais phenyl. In some embodiments, Rais an optionally substituted heteroaryl group. In some embodiments, Rais an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rais an optionally substituted C2-20 carbonate. In some embodiments, Rais -C(O)ORc. In some embodiments, Rais an optionally substituted C2-20carbamate. In some embodiments, Rais -C(O)N(Rc)2. In some embodiments, Rais an optionally substituted C2-20 thioester. In some embodiments, Rais -C(S)Rc. In some embodiments, Rais an optionally substituted C2-20 thiocarbonate. In some embodiments, Rais -C(S)ORc. In some embodiments, Rais an optionally substituted C2-20dithiocarbonate. In some embodiments, Rais -C(S)SRc. In some embodiments, Rais an optionally substituted C1-20 thiocarbamate. In some embodiments, Rais -C(S)N(Rc)2.

[0062] In some embodiments, Rais an optionally substituted hydroxyl protecting group. Suitable hydroxyl protecting groups are well known in the art and include those described in detail in Protecting Groups in Organic Synthesis, T. W. Greene and P. G. M. Wuts, 3rdedition, John Wiley & Sons, 1999. Examples of suitable oxygen protecting groups include, but are not limited to, acetyl, benzoyl benzyl, β-methoxyethoxymethyl ether (MEM), dimethoxytrityl 18 409753-015WO (210651) BUSINESS.31699770.1 (DMT), methoxymethyl ether (MOM), methoxytrityl (MMT), p-methoxybenzyl ether (PMB), methylthiomethyl ether, pivaloyl, tetrahydropyranyl (THP), tetrahydrofuran (THF), trityl, silyl ethers (e.g., trimethylsilyl (TMS), tert-butyldimethylsilyl (TBDMS), tri-iso-propylsilyloxymethyl (TOM), and triisopropylsilyl (TIPS) ethers), methyl ethers, and ethoxyethyl ethers. In some embodiments, Rais -ORc.

[0063] In some embodiments, Rais an optionally substituted phosphorous-linked functional group. It will be appreciated that “phosphorous-linked functional group” as used herein refers to moieties that comprise one or more phosphorous atoms (e.g., phosphine, phosphodiester, phosphonic acid, phosphate). In some embodiments, Rais an optionally substituted sulfur-linked functional group. It will be appreciated that “sulfur-linked functional group” as used herein refers to moieties that comprise one or more sulfur atoms (e.g., thioether, sulfone, sulfonic acid, sulfoxide, thiol, thiocyanate, or disulfide). In some embodiments, Rais an optionally substituted silicon-linked functional group. It will be appreciated that “silicon-linked functional group” as used herein refers to moieties that comprise one or more silicon atoms (e.g., silanol, suloxides, siloxanes, silyl ethers, silyl chlorides, silyl hydrides, silenes, or siloles).

[0064] In some embodiments, Rais an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rais an optionally substituted polymer chain. In some embodiments, Rais a linkage via a bond or a carbon- containing linker moiety to an ascaroside molecule. In some embodiments, Rais an optionally substituted C1-6aliphatic or heteroaliphatic comprising an ascaroside.

[0065] In some embodiments, Rbis an optionally substituted C1-20aliphatic. In some embodiments, Rbis an optionally substituted C1-6 aliphatic. In some embodiments, Rbis C1-20 aliphatic. In some embodiments, Rbis C1-6 aliphatic. In some embodiments, Rbis methyl, ethyl, n-propyl, iso-propyl, n-butyl, isobutyl, sec-butyl, or t-butyl. In some embodiments, Rbis C1-20acyl. In some embodiments, Rbis -C(O)Rc. In some embodiments, Rbis -C(O)H. In some embodiments, Rbis -C(O)CH3. In some embodiments, Rbis an optionally substituted C1-20 heteroaliphatic. In some embodiments, Rbis an optionally substituted C1-6heteroaliphatic. In some embodiments, Rbis C1-20 heteroaliphatic. In some embodiments, Rbis C1-6 heteroaliphatic. In some embodiments, Rbis an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, 19 409753-015WO (210651) BUSINESS.31699770.1 or sulfur. In some embodiments, Rbis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis optionally substituted aryl. In some embodiments, Rbis optionally substituted phenyl. In some embodiments, Rbis phenyl. In some embodiments, Rbis an optionally substituted heteroaryl group. In some embodiments, Rbis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rbis an optionally substituted C2-20 carbonate. In some embodiments, Rbis -C(O)ORc. In some embodiments, Rbis an optionally substituted C2-20carbamate. In some embodiments, Rbis -C(O)N(Rc)2. In some embodiments, Rbis an optionally substituted C2-20 thioester. In some embodiments, Rbis -C(S)Rc. In some embodiments, Rbis an optionally substituted C2-20 thiocarbonate. In some embodiments, Rbis -C(S)ORc. In some embodiments, Rbis an optionally substituted C2-20dithiocarbonate. In some embodiments, Rbis -C(S)SRc. In some embodiments, Rais an optionally substituted C1-20 thiocarbamate. In some embodiments, Rbis -C(S)N(Rc)2.

[0066] In some embodiments, Rbis an optionally substituted hydroxyl protecting group. In some embodiments, Rbis -ORc.

[0067] In some embodiments, Rbis an optionally substituted phosphorous-linked functional group. In some embodiments, Rbis an optionally substituted sulfur-linked functional group. In some embodiments, Rbis an optionally substituted silicon-linked functional group.

[0068] In some embodiments, Rbis an optionally substituted sugar moiety. In some embodiments, Rais an optionally substituted peptide. In some embodiments, Rbis an optionally substituted polymer chain. In some embodiments, Rbis a linkage via a bond or a carbon- containing linker moiety to an ascaroside molecule. In some embodiments, Rbis an optionally substituted C1-6 aliphatic or heteroaliphatic comprising an ascaroside.

[0069] In some embodiments, Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 3- to 12- membered monocyclic or bicyclic saturated or partially unsaturated 20 409753-015WO (210651) BUSINESS.31699770.1 carbocyclyl or heterocyclyl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Raand Rbmay be taken together to form an optionally substituted 5- to 12-membered monocyclic or bicyclic aryl or heteroaryl ring having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0070] In certain embodiments, Rais -H and Rbis p-hydroxybenzoate. In certain embodiments, Rais -H and Rbis indole-3-carboxylate. In certain embodiments, Rais -H and Rbis (E)-2-methyl- 2-butenoate. In certain embodiments, Rais -H and Rbis picolinate. In certain embodiments, Rais -H and Rbis nicotinate. In certain embodiments, Rais -H and Rbis (R)-2-hydroxy-2-(4- hydroxyphenyl)ethyl)amino)-4-oxobutanoate. In certain embodiments, Rais -H and Rbis 4-((4- hydroxyphenethyl)amino)-4-oxobutanoate.

[0071] In certain embodiments Raand Rbare both -H, and Z is selected from the formulae defined in (i) to (ix) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (i) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (iv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (v) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (vi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (vii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (viii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (ix) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (x) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiii) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xiv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xv) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvi) above. In certain embodiments Raand Rbare both -H, and Z conforms to formula (xvii) above.

[0072] As defined above and described herein, each Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-1221 409753-015WO (210651) BUSINESS.31699770.1 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule.

[0073] In some embodiments, Rcis independently at each occurrence selected from -H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl.

[0074] In some embodiments, an occurrence of Rcis -H. In some embodiments, Rcis an optionally substituted C1-12aliphatic group. In some embodiments, Rcis an optionally substituted C1-6 aliphatic group. In some embodiments, Rcis an optionally substituted C1-12 heteroaliphatic group. In some embodiments, Rcis an optionally substituted C1-6 heteroaliphatic group. In some embodiments, Rcis an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted aryl group. In some embodiments, Rcis optionally substituted phenyl. In some embodiments, R2is phenyl. In some embodiments, Rcis an optionally substituted heteroaryl group. In some embodiments, Rcis an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, Rcis an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0075] As defined above and described herein, R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a glycoside, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, or an optionally substituted aromatic group, an optionally substituted heteroaryl group.

[0076] In some embodiments, R2is -H. In some embodiments, R2is a metal cation. In certain embodiments, R2is an organic cation (e.g. a nitrogen or phosphorous centered cationic group). In some embodiments, R2is an optionally substituted C1-20aliphatic group. In certain 22 409753-015WO (210651) BUSINESS.31699770.1 embodiments, R2is an optionally substituted C1-12aliphatic group. In certain embodiments, R2is an optionally substituted C1-8 aliphatic group. In certain embodiments, R2is an optionally substituted C1-6 aliphatic group. In certain embodiments, R2is selected from methyl, ethyl, n- propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In some embodiments, R2is an optionally substituted C1-6 aliphatic group. In some embodiments, R2is an optionally substituted C1-20 heteroaliphatic group. In some embodiments, R2is an optionally substituted C1-6 heteroaliphatic group. In some embodiments, R2is an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted aromatic group. In some embodiments, R2is optionally substituted phenyl. In some embodiments, R2is phenyl. In some embodiments, R2is an optionally substituted heteroaryl group. In some embodiments, R2is an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R2is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0077] In some embodiments, R2is a glycoside. It will be appreciated that a glycoside refers to a moiety comprising a sugar bound to another functional group via a glycosidic bond.

[0078] In some embodiments, R2is nucleotide. In some embodiments, R2is adenosine monophosphate, cytidine monophosphate, guanosine monophosphate, or uridine monophosphate. In some embodiments, R2is deoxyadenosine monophosphate, deoxycytidine monophosphate, deoxyguanosine monophosphate, or deoxythymidine monophosphate.

[0079] In some embodiments, R2is a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, R2is an optionally substituted C1-6 aliphatic or heteroaliphatic comprising an ascaroside.

[0080] In certain embodiments, R2comprises an amino acid. In certain embodiments, R2comprises a peptide.

[0081] As defined above and described herein, each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an 23 409753-015WO (210651) BUSINESS.31699770.1 optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. In some embodiments, each R3is independently selected from -H and C1-8aliphatic. In some embodiments, one R3is -H and the other R3is other than -H. In some embodiments, neither R3is -H. In some embodiments, each R3is -H. In some embodiments, an occurrence of R3is an optionally substituted C1-20 aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-6aliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-20 heteroaliphatic group. In some embodiments, an occurrence of R3is an optionally substituted C1-6 heteroaliphatic group. In some embodiments, R3is an optionally substituted 3- and 8-membered saturated or partially unsaturated heterocyclyl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- and 12-membered saturated or partially unsaturated bicyclic heterocyclyl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, occurrence of R3is an optionally substituted aryl group. In some embodiments, R3is optionally substituted phenyl. In some embodiments, R3is phenyl. In some embodiments, R3is an optionally substituted heteroaryl group. In some embodiments, R3is an optionally substituted 5- to 6-membered heteroaryl having 1-3 heteroatoms independently selected from nitrogen, oxygen, or sulfur. In some embodiments, R3is an optionally substituted 8- to 12-membered heteroaryl having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0082] In certain embodiments, at least one R3is -H. In certain embodiments, both R3groups are -H. In certain embodiments, at least one R3is an optionally substituted C1-20 aliphatic group. In certain embodiments, both R3groups are an optionally substituted C1-20 aliphatic group which may be the same or different. In certain embodiments, at least one R3is an optionally substituted C1-12 aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-8 aliphatic group. In certain embodiments, at least one R3is an optionally substituted C1-6 aliphatic group. In certain embodiments, at least one R3is selected from methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl, and t-butyl. In certain embodiments, at least one R3is -CH2CH2OH. In certain embodiments, at least one R3is -CH2CH2OR2. where R2is as defined in the genera and subgenera herein. In certain embodiments, at least one R3is an optionally substituted aromatic group. In certain embodiments, at least one R3comprises a glycoside. In certain embodiments, at 24 409753-015WO (210651) BUSINESS.31699770.1 least one R3comprises an amino acid. In certain embodiments, at least one R3at least one R3comprises a peptide. In certain embodiments, at least one R3comprises a nucleotide.

[0083] In certain embodiments, an ascaroside is selected from the group consisting of: CO O2R2CO2R2CO x O x O2R2CO O2R2x x in the genera and subgenera herein.

[0084] In certain embodiments, an ascaroside is selected from the group consisting of: CO2H CO2H C CO2H O O x O x O2H O x x

[0085] In certain embodiments, an ascaroside is selected from the group consisting of: CO O2R2y CO2R2CO2R2CO O2R2 in the genera and subgenera herein.

[0086] In certain embodiments, an ascaroside is selected from the group consisting of: CO2H CO2H CO2H

[0087] In certain embodiments, an ascaroside is selected from the group consisting of: CO2R2 25 409753-015WO (210651) BUSINESS.31699770.1

[0088] In certain embodiments, an ascaroside is selected from the group consisting of: CO2H CO2H CO CO2H O2H x O x O O x x

[0089] In certain embodiments, an ascaroside is selected from the group consisting of: CO R2O2y CO2R2CO R2CO2R2O y O2O y

[0090] In certain embodiments, an ascaroside is selected from the group consisting of: CO O2H y CO CO H O2H CO2H O2

[0091] In certain embodiments, an ascaroside is selected from the group consisting of: herein.

[0092] In certain embodiments, an ascaroside is selected from the group consisting of:

[0093] In certain embodiments, an ascaroside is selected from the group consisting of: 26 409753-015WO (210651) BUSINESS.31699770.1 nera herein.

[0094] In certain embodiments, an ascaroside is selected from the group consisting of:

[0095] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I), where Z is –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0096] In an embodiment, ascarosides useful in the context of the present disclosure have the general structure (I) where Z is –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

[0097] Specific ascarosides that are useful in the context of the present disclosure include, but are not limited to, ascr#7 and ascr#18. is selected from the group consisting of: ascr#9, ascr#12, ascr#14, ascr#1, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, ascr#24, ascr#26, ascr#28, ascr#30, ascr#32, ascr#34, and ascr#36. In certain embodiments, an ascaroside used in the provided methods is selected from the group consisting of: ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24. In certain embodiments, 27 409753-015WO (210651) BUSINESS.31699770.1 an ascaroside used in the provided methods is selected from the group consisting of: ascr#9, ascr#14, ascr#10, and ascr#18.

[0099] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, an ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22. In certain embodiments, an ascaroside used in the provided methods is selected from the group consisting of: bhas#5, oscr#9, oscr#12, oscr#1, oscr#14, oscr#10, oscr#16, oscr#18, oscr#20, oscr#22, oscr#24, oscr#26, oscr#28, oscr#30, oscr#32, oscr#34, and oscr#36. In certain embodiments, an ascaroside used in the provided methods is selected from the group consisting of: oscr#10, oscr#16, oscr#18, oscr#20, and oscr#22.

[0100] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhas#9, bhas#10, bhas#16, bhas#18, bhas#22, bhas#24, bhas#26, bhas#28, bhas#30, bhas#32, bhas#34, bhas#36, bhas#38, bhas#40, and bhas#42.

[0101] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: bhos#10, bhos#16, bhos#18, bhos#22, bhos#24, bhos#26, bhos#28, bhos#30, bhos#32, bhos#34, bhos#36, bhos#38, bhos#40, and bhos#42.

[0102] In certain embodiments, an ascaroside used in the provided methods and compositions is selected from the group consisting of: ascr#18, oscr#16, oscr#17, oscr#15, bhas#18, bhos#16, glas#18, dhas#18, ibha#18, ibho#16, icas#18, icos#15, icos#16, and any combination of two or more of these. In certain embodiments, an ascaroside used in the provided methods and compositions is ascr#18. In certain embodiments, an ascaroside used in the provided methods and compositions is oscr#16.

[0103] Ascarosides can be obtained from natural sources (e.g., nematodes) or they may be prepared synthetically. Ascarosides can be prepared synthetically, for example, by converting 1- O-substituted rhamnose to 1-O-substituted ascarylose. An exemplary method of preparing ascarosides includes: providing as a feedstock a 1-O-substituted rhamnose; forming a mono- sulfonate ester at the 3-OH group of the feedstock; and treating the mono-sulfonate ester with a hydride source to form a 1-O-substituted ascarylose. In certain embodiments, forming the mono- sulfonate ester is conducted on a substrate without hydroxyl protecting groups at the 2- or 4- 28 409753-015WO (210651) BUSINESS.31699770.1 position of the rhamnose feedstock. In certain embodiments, such methods comprise contacting the feedstock with a sulfonating agent (i.e., a sulfonyl halide, sulfonic anhydride or similar reagent) in the presence of a Lewis acid. Specific details regarding the synthesis of 1-O- substituted ascarylose can be found in international publication No. WO 2022 / 024067, which is incorporated herein by reference.

[0104] As indicated, according to the present disclosure, ascarosides are used in combination with plant nutrients. The term “plant nutrients” as used herein encompasses compounds comprising essential or beneficial elements for plant growth and / or development. “Essential” elements are generally considered to be those that are required to allow for the life cycle of a plant species. “Beneficial” elements may not meet the criteria of essentiality but can benefit plant growth and development or can benefit the quality attributes of a plant or its harvested product. Plant nutrients include elements for which a clear plant metabolic function has been identified, as well as elements that have demonstrated clear benefits to plant productivity, crop quality, resource use efficiency, stress tolerance and / or pest and disease resistance.

[0105] In some embodiments, plant nutrients are mineral plant nutrients. Compounds and compositions suitable for use in various embodiments of the present disclosure may comprise one or more of the following: primary nutrients (nitrogen (N), phosphorus (P), and / or potassium (K), often referred to as the “NPK nutrients”); secondary nutrients (calcium (Ca), magnesium (Mg), and sulfur (S)); and / or trace nutrients (including, but not limited to, boron (B), chlorine (Cl), copper (Cu), iron (Fe), manganese (Mn), molybdenum (Mo), and zinc (Zn)). These nutrient classifications (primary, secondary, and trace) are related primarily to the amount of each nutrient needed; primary nutrients are needed in relatively large quantities, secondary nutrients are needed in smaller quantities, and trace nutrients are needed in rather small quantities. The primary and secondary nutrients are sometimes referred to as “macronutrients,” and the trace nutrients are sometimes referred to as “micronutrients.”

[0106] Although not intending to be limited by theory, it is generally understood that nitrogen (N) is a key element in plant / vegetative growth and in particular, can promote good stalk growth. Compounds capable of providing N and thus serving as plant nutrients according to the present disclosure include, but are not limited to, ammonium sulfate, ammonium nitrate, and urea.

[0107] Although not intending to be limited by theory, it is generally understood that phosphorus (P) can strengthen a plant’s root systems, capacity for seed creation, disease resistance, and pest 29 409753-015WO (210651) BUSINESS.31699770.1 resistance, and improve flowers / blooming and strengthen tissues and flavors in edible plants and vegetables. Phosphorus sources include, but are not limited to, superphosphate (made from rock phosphate and sulfuric acid). Manure from grain-fed animals is another common phosphorus source.

[0108] Although not intending to be limited by theory, it is generally understood that potassium (K) increases plant vigor and disease resistance, helps form and move starches, sugars, and oils in plants, can improve flowering and growth of fruit / fruit quality, and is also important for roots and seed production. Sources of potassium include, but are not limited to, muriate of potash and sulfate of potash, as well as wood ash and banana peels.

[0109] These three primary macronutrients (P, N, and K) may, in some embodiments, be applied via a nutrient-rich composition that comprises two or three of these primary nutrients. Such nutrient-rich compositions include, but are not limited to, manures or guano, fish emulsion, bone meal, blood meal, biofertilizers, and cover crops.

[0110] The NPK ratio of such nutrient-rich compositions can vary. In some embodiments, a nutrient mixture with equivalent N, P, and K values is employed (e.g., a formulation with a 6-6-6 N-P-K ratio). In some embodiments, a nutrient mixture with a comparatively higher ratio of N is employed (e.g., a formulation with a 20-6-6 N-P-K ratio). Nutrient mixtures with other NPK ratios can be employed; the NPK ratios relevant according to the present disclosure are not particularly limited. As further examples, a good formula for promoting rooting and post- transplanting care may be a formulation with a 6-20-20 N-P-K ratio and a good formula for supporting and protecting flower development may be a formulation with a 6-20-6 N-P-K ratio. A formula for grasses may have a high “N” value, e.g., with a 30-0-0 N-P-K ratio. Generally, any nutrient mixture with any NPK ratio suitable for a given plant at a given stage of plant growth under given conditions is employed along with an ascaroside as provided herein.

[0111] Although not intending to be limited by theory, it is generally understood that calcium (Ca) strengthens and fortifies overall plant tissues and helps neutralize acidity within the plant (thereby acting as a detoxifying agent by neutralizing organic acids therein) and in the surrounding soil (particularly when limed, improving crop yields). Calcium activates several enzyme systems in protein synthesis and carbohydrate transfer. It is involved in the formation of the plant cell wall membrane and its plasticity. In peanuts, calcium is essential for seed production. Sources of calcium include, but are not limited to, gypsum. 30 409753-015WO (210651) BUSINESS.31699770.1

[0112] Although not intending to be limited by theory, it is generally understood that magnesium (Mg) helps increase intake of phosphorus and boost production of chlorophyll, giving a healthy green color to the plant and encouraging absorption of CO2. Magnesium is also a co-factor in several enzyme reactions that activate phosphorylation and is required to stabilize ribosome particles and to stabilize the structure of nucleic acids. Further, magnesium as a role in assisting the movement of sugars within a plant. Sources of magnesium include, but are not limited to, garden lime (e.g., dolomitic lime, which has high magnesium levels or calcific lime, which has high calcium).

[0113] Although not intending to be limited by theory, it is generally understood that sulfur (S) is actively involved in metabolism of biotin and thiamine and co-enzyme A and aids in production of seeds, formation of chlorophyll, formation of nodules in legumes, and stabilization of protein structures.

[0114] Although not intending to be limited by theory, it is generally understood that boron (B) can promote root growth and is essential for pollen germination and growth of the pollen tube, Boron has been associated with lignin synthesis, activities of certain enzymes, seed and cell wall formation, and sugar transport within the plant.

[0115] Although not intending to be limited by theory, it is generally understood that chlorine (Cl) is essential in photosynthesis (as it is involved in the evolution of oxygen). Chlorine increases cell osmotic pressure and the water content of plant tissues.

[0116] Although not intending to be limited by theory, it is generally understood that copper (Cu) is essential in several plant enzyme systems involved in photosynthesis. It may play a role in the synthesis and / or stability of chlorophyll and other plant pigments.

[0117] Although not intending to be limited by theory, it is generally understood that iron (Fe) is essential in the heme enzyme system in plant metabolism (affecting photosynthesis and respiration). It is understood to be essential in the synthesis and maintenance of chlorophyll in plants and is believed to be strongly associated with protein metabolism.

[0118] Although not intending to be limited by theory, it is generally understood that manganese (Mn) primarily functions as part of the plant enzyme system, activating several metabolic functions and is also involved in the oxidation-reduction process of photosynthesis. It has further been demonstrated to activate indole acetic acid oxidase, which then oxidizes indole acetic acid in plants. 31 409753-015WO (210651) BUSINESS.31699770.1

[0119] Although not intending to be limited by theory, it is generally understood that molybdenum (Mb) is an important component of two major enzymes in plants required for normal assimilation of nitrogen and is required by some soil microorganisms for nitrogen fixation in soils.

[0120] Although not intending to be limited by theory, it is generally understood that zinc (Zn) is required for the synthesis of tryptophan, which in turn is required for the formation of indole acetic acid in plants and is also an essential component of several metallo-enzymes in plants. Zn also activates the enzyme carbonic anhydrase and has a role in RNA and protein synthesis in plants.

[0121] It is noted that, while the application focuses on the application of ascarosides in combination with one or more plant nutrients, the ascaroside can alternatively (or in addition) be applied along with one or more general soil amendments which can function, e.g., to enhance the ability of nutrients to be absorbed by the plants. Such general soil amendments include, but are not limited to, compost, mulch, worm castings, wood ash, lime, and other natural additions that enhance nutrient use and availability.

[0122] The method provided herein comprises applying a combination of an effective amount of one or more ascarosides and an effective amount of one or more plant nutrients to a seed, a plant, plant foliage, or to the soil where the plant is grown. According to the disclosure, in some embodiments, the one or more plant nutrients and one or more ascarosides can be applied at the relevant time(s) for plant nutrient application (e.g., when a nutrient deficiency is suspected / confirmed for a given plant or crop). Advantageously, an ascaroside can provide long- lasting effects for prevention of pathogen damage to the crop and as such, can be applied at various stages conveniently along with the one or more nutrient(s). Thus, in certain embodiments provided herein, to provide nutrients and pathogen protection to a plant, these components can be applied at a single time point, corresponding to a required time point to ensure the plant nutrient balance is sufficient.

[0123] The application of the one or more nutrients and the one or more ascarosides can be in pre- or post-emergence application. The preferred application method depends on the usual or optimal application time of the particular nutrient(s). Typically, nutrients are added to plants during the growth period and / or during the blooming period of the plant. The timing of applying the nutrient(s) and ascaroside(s) according to the present disclosure can, in some embodiments, 32 409753-015WO (210651) BUSINESS.31699770.1 be crop-specific. Higher values of some of these nutrients are more necessary at some times than others. It is noted that plant nutrients may be applied more than one time during the growing period (which plant nutrients can be the same or, more commonly, different); the one or more ascarosides can be applied with the relevant plant nutrients at one of these nutrient applications or more than one of these applications. For example, in some embodiments, the one or more ascarosides are applied along with the first application of a given plant nutrient (e.g., during the seedling stage). In some embodiments, the one or more ascarosides are applied along with a final application of a given plant nutrient.

[0124] In some embodiments, the disclosure provides a method of applying a macronutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a micronutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a nitrogen-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a potassium-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a phosphorus- containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a nitrogen-containing plant nutrient and a potassium-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a nitrogen-containing plant nutrient and a phosphorus-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a phosphorus-containing plant nutrient and a potassium-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a nitrogen-containing plant nutrient, a phosphorus-containing plant nutrient, and a potassium-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a calcium-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a magnesium- containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a sulfur-containing plant nutrient in combination with one or more ascarosides. 33 409753-015WO (210651) BUSINESS.31699770.1

[0125] In some embodiments, the disclosure provides a method of applying a boron-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a chlorine-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a copper- containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying an iron-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a manganese-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a molybdenum-containing plant nutrient in combination with one or more ascarosides. In some embodiments, the disclosure provides a method of applying a zinc-containing plant nutrient in combination with one or more ascarosides.

[0126] In some embodiments, methods provided herein can comprise monitoring the plant and / or the soil surrounding a growing plant to evaluate nutrient levels and applying appropriate nutrient(s) in combination with one or more ascarosides based on the results of such monitoring.

[0127] In some embodiments, such monitoring comprises simply evaluating the look of the plant, as a lack or imbalance of nutrients can often be determined based on a few universal signs. For example, a nitrogen deficiency may result in light green and / or yellowish foliage on the affected plant (typically appearing first on older leaves and then on younger leaves as the deficiency becomes more severe); slower, stunted growth of the plant; and shedding of older leaves in some plants. A phosphorus deficiency may result in an overall stunted plant and with a severe deficiency, abnormally dark green leaves (old growth) may be present and / or dead areas may be present on the leaves (typically affecting older leaves before younger leaves), as well as fruit and stems of the plant. A purple or reddish color may be observed on the leaves of deficient corn plants. A phosphorus deficiency can further result in a lack of flowering / dropped flowers and / or a burnt leaf tip appearance. A potassium deficiency may result in yellowing along the leaf margins of older leaves of an affected plant. Plants deficient in potassium grow slowly and have poorly developed root systems and weak stalks and as such, plants commonly fall over in potassium-deficient plants. Wilted old growth may also signal a potassium deficiency. A calcium deficiency may cause poor root growth and in severe cases, the growing point may die. Calcium- 34 409753-015WO (210651) BUSINESS.31699770.1 deficient roots often turn black and rot; the plant may develop symptoms at young leaves and the growing points of shoots and the plant may exhibit gelatinous leaf tips. A magnesium deficiency can result in the development of a yellowish, bronze, or reddish color in the leaves, while the leaf veins remain green (typically appearing first on the lower, older leaves). A calcium deficiency may cause blossom end rots (on fruit such as tomatoes).

[0128] In some embodiments, such monitoring comprises evaluating soil content of various nutrients via soil testing. It is noted that soil tests for nitrogen are commonly inaccurate due to the high mobility of nitrogen in soil. However, soil tests for the other nutrients may provide relevant information as to the nutrients to advantageously be applied to the plants grown in such soil to optimize the plant growth and corresponding properties. This analysis may provide insight on placement and timing of nutrient application. Suitable tests can comprise, e.g., processing a soil sample via extraction and analyzing the resulting extract via one or more analytical methods including, but not limited to, laser scanning confocal microscopy, mass spectroscopy, digestion, combustion, and other methods. In some embodiments, such monitoring comprises foliar testing for various nutrients.

[0129] The anti-pathogen activity of ascarosides provides additional benefits to the methods and compositions provided herein. Advantageously and conveniently, by applying one or more ascarosides in combination with one or more plant nutrients, it is possible to remove a step of antimicrobial (e.g. fungicide, antibiotic, antiviral, or anti-helminth) application (e.g., later during the growth cycle of the plant) due to the long-lasting effect afforded by the ascaroside(s). For example, although fungicides and antibacterial agents are generally applied at later time points in crop growth when such pathogens are present, the present disclosure provides methods and compositions which employ application of an ascaroside at a very early time point (i.e., a time point at which one or more nutrients are applied to crops) and can impart resistance to pathogens in the crop plants so treated. In some embodiments, although applying the ascaroside at an early stage in the plant life cycle, it surprisingly exhibits a long-lasting effect, e.g., decreasing or preventing damage caused by fungi, bacteria, viruses and molds for a period of time exceeding 3 days after application, exceeding 5 days after application, exceeding one week after application, exceeding two weeks after application, exceeding one-month after application, exceeding two- months after application, or exceeding three-months after application. 35 409753-015WO (210651) BUSINESS.31699770.1

[0130] The co-application of one or more nutrients and one or more ascarosides at a single time point (e.g., including, but not limited to, early in the season) can also provide important economic advantages to growers and enhance the sustainability of crop production. Co- application of ascarosides with the one or more nutrients can prevent the need for a separate fungicide or antimicrobial treatment later in the season. This saves fuel and labor and potentially avoids the need to apply more toxic pathogen control products since ascaroside treatments can act as a preventative control that enhances crops’ tolerance to a broad range of pathogens. An additional or alternate benefit of combining ascarosides with one or more nutrients is the control of early season plant pathogens such as fungi, bacteria, viruses and nematodes. Co-application of ascarosides with one or more nutrients can prevent the need for a separate early season disease control application (e.g. of a fungicide, antimicrobial, or nematicide) which saves fuel and labor and potentially avoids the need to apply more toxic pathogen control products since ascaroside treatments can act as a preventative control that enhances crops’ tolerance to a broad range of pathogens.

[0131] In certain embodiments, the disclosure provides blends or compositions of one or more plant nutrients and one or more ascarosides. In certain embodiments, the disclosure provides blends of one or more plant nutrients and one or more ascarosides, characterized in that the blended product provides nutrients to the plant and also protects the plants from pathogens. In certain embodiments, the disclosure provides blends or compositions of one or more plant nutrients and one or more ascarosides wherein treatment with said blend increases the yield relative to plants treated with nutrients alone by at least about 5%, at least about 10%, at least about 15%, at least about 20%, at least about 25%, at least about 30%, at least about 35%, at least about 40%, at least about 50%, at least about 60%, at least about 75%, or at least about 90%. In certain embodiments, the disclosure provides blends or compositions of one or more plant nutrients and one or more ascarosides wherein treatment with said blend increases the yield relative to plants treated with nutrients alone by between 0 and about 5%, between about 5% and about 10%, between about 10% and about 15%, between about 15% and about 20%, between about 20% and about 25%, between about 25% and about 30%, between about 30% and about 35%, between about 35% and about 40%, between about 40% and about 50%, between about 50% and about 60%, between about 60% and about 75%, or between about 75% and about 90%. In certain embodiments, the disclosure provides blends or compositions of one or more plant 36 409753-015WO (210651) BUSINESS.31699770.1 nutrients and one or more ascarosides wherein treatment with said blend increases the yield relative to plants treated with nutrients alone by about 5%, about 10%, about 15%, about 20%, about 25%, about 30%, about 35%, about 40%, about 50%, about 60%, about 75%, or about 90%.

[0132] The compounds described herein (i.e., the plant nutrient(s) and the ascaroside(s)) can be provided in a single formulation or agricultural composition or in separate formulations or agricultural compositions. Additionally, the components may be applied separately. When the one or more ascarosides and the one or more plant nutrients are applied separately, the one or more ascarosides can be applied before or after the application of the one or more plant nutrients. Generally, when applied separately, the components are co-applied at close points in time, e.g., substantially simultaneously or within about several minutes or hours, including within about 5 minutes, within about 10 minutes, within about 30 minutes, within about an hour, within about 2 hours, within about 3 hours, within about 4 hours, within about 6 hours, within about 7 hours, within about 8 hours, within about 24 hours, or within about 2 days of one another).

[0133] Co-application, can, in some embodiments, involve combining the one or more ascarosides and the one or more plant nutrients before application (e.g., immediately prior to application) to the plants. The one or more ascarosides and the one or more plant nutrients may be mixed in the field; for example, the one or more ascarosides can be added to a fully formulated tank mix comprising the one or more plant nutrients.

[0134] In other embodiments, the components to be co-applied can be combined at a timepoint further in advance of application. In such embodiments, an agricultural formulation is prepared comprising one or more ascarosides and the one or more plant nutrients in combination with one or more inert ingredients. Advantageously, in such combinations, the one or more ascarosides and the one or more plant nutrients are compatible with one another, and the resulting formulations can demonstrate stability over long periods of time (e.g., about one week or more, about one month or more, about two months or more, about three months or more, about four months or more, about five months or more, or about six months or more).

[0135] The one or more ascarosides and the one or more plant nutrients can be formulated together in a combination formulation. As noted above, the formulations or methods can include other active ingredients and / or plant or plant product treatment compounds. Further, some of the 37 409753-015WO (210651) BUSINESS.31699770.1 compositions will be residual in that they do not easily wash off the leaves during rain, and thus can protect plants during and after rainy weather.

[0136] In certain embodiments, the disclosure provides blends of one or more plant nutrients and one or more ascarosides where a weight ratio of plant nutrient(s) to ascaroside is greater than 100:1, greater than 500:1 or greater than 1000:1. In certain embodiments, the disclosure provides blends of a plant nutrient and an ascaroside where a weight ratio of plant nutrient(s) to ascaroside is greater than 1500:1, greater than 2000:1, greater than 3000:1, greater than 5000:1, greater than 7500:1, greater than 10,000:1, greater than 15,000:1, greater than 20,000:1, greater than 30,000:1, greater than 50,000:1, greater than 100,000:1, greater than 500,000:1, greater than 1,000,000:1, greater than 2,000,000:1, greater than 5,000,000:1, or greater than 10,000,000:1.

[0137] In certain embodiments, provided compositions comprise formulations that are intended for application to crops such that their foliar application to crops will deliver between about 1 mg and about 1,000 mg of one or more ascarosides per acre in combination with an effective amount of one or more plant nutrients. In certain embodiments, such compositions are formulated for application such that they deliver between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25-100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre.

[0138] In certain embodiments, provided compositions are formulated such that their foliar application to crops delivers between about 1 mg and about 1000 mg of one or more ascarosides per acre in combination with a nitrogen plant nutrient at a rate of at least 2 oz per acre. In certain such embodiments, compositions are formulated for application such that they deliver between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25-100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 4 oz of nitrogen per acre, at least 8 oz of nitrogen per acre, at least 1 pound of nitrogen per acre, at least 2 pounds of nitrogen per acre, at least 5 pounds of nitrogen per acre, or at least 10 pounds of nitrogen per acre.

[0139] In certain embodiments, provided compositions are formulated such that their foliar application to crops delivers between about 1 mg and about 1000 mg of one or more ascarosides per acre in combination with a potassium plant nutrient at a rate of at least 2 oz per acre. In certain such embodiments, compositions are formulated for application such that they deliver 38 409753-015WO (210651) BUSINESS.31699770.1 between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25- 100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 4oz of potassium per acre, at least 8oz of potassium per acre, at least 1 pound of potassium per acre, at least 2 pounds of potassium per acre, at least 5 pounds of potassium per acre, or at least 10 pounds of potassium per acre.

[0140] In certain embodiments, provided compositions are formulated such that their foliar application to crops delivers between about 1 mg and about 1000 mg of one or more ascarosides per acre in combination with a phosphorus plant nutrient at a rate of at least 1 oz per acre. In certain such embodiments, compositions are formulated for application such that they deliver between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25- 100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 2 oz of phosphorus per acre, at least 4 oz of phosphorus per acre, at least 8 oz of phosphorus per acre, at least 1 pound of phosphorus per acre, at least 2 pounds of phosphorus per acre, at least 5 pounds of phosphorus per acre, or at least 10 pounds of phosphorus per acre.

[0141] In certain embodiments, formulations deliver ascaroside(s) in combination with any two or more of nitrogen, sulfur, or phosphorus at any combination of the rates described above or herein. In certain embodiments, formulations deliver ascaroside(s) in combination with any two or more of nitrogen, potassium, or phosphorus at any combination of the rates described above or herein.

[0142] In certain embodiments, provided compositions are formulated such that their foliar application to crops delivers between about 1 mg and about 1000 mg of one or more ascarosides per acre in combination with an effective amount of a sulfur, calcium, or magnesium plant nutrient. In certain such embodiments, compositions are formulated for application such that they deliver between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25-100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 0.1oz of sulfur per acre, at least 0.5 oz of sulfur per acre, at least 1 oz of sulfur per acre, at least 2 oz of sulfur per 39 409753-015WO (210651) BUSINESS.31699770.1 acre, at least 4 oz of sulfur per acre, at least 8 oz of sulfur per acre, at least 1 pound of sulfur per acre, at least 2 pounds of sulfur sulfur per acre, at least 5 pounds of sulfur per acre, or at least 10 pounds of sulfur per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 0.1 oz of calcium per acre, at least 0.5 oz of calcium per acre, at least 1 oz of calcium per acre, at least 2 oz of calcium per acre, at least 4 oz of calcium per acre, at least 8 oz of calcium per acre, or at least 1 pound of calcium per acre. In certain such embodiments, compositions are formulated for application such that they deliver at least 0.1 oz of magnesium per acre, at least 0.5 oz of magnesium per acre, at least 1 oz of magnesium per acre, at least 2 oz of magnesium per acre, at least 4 oz of magnesium per acre, at least 8 oz of magnesium per acre, or at least 1 pound of magnesium per acre. In certain embodiments, such formulations deliver ascaroside(s) in combination with any two or more of sulfur, calcium and magnesium at any combination of the rates described above.

[0143] In certain embodiments, provided compositions are formulated such that their foliar application to crops delivers between about 1 mg and about 1000 mg of one or more ascarosides per acre in combination with an effective amount of one or more plant micronutrients. In certain such embodiments, compositions are formulated for application such that they deliver between 1-10 mg of ascaroside per acre, between 5-25 mg of ascaroside per acre, between 25-100 mg of ascaroside per acre, between about 100 and 500 mg of ascaroside per acre, or between 500-1,000 mg of ascaroside per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of zinc in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of zinc per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of iron in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of iron per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of manganese in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of manganese per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of boron in addition to the 40 409753-015WO (210651) BUSINESS.31699770.1 ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of boron per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of silicon in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of silicon per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of copper in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, at least 4 oz, or at least 8 oz of copper per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of molybdenum in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, or at least 4 oz, or at least 8 oz of molybdenum per acre. In certain such embodiments, compositions are formulated for application such that they deliver an effective amount of nickel in addition to the ascaroside. In certain embodiments, such compositions are formulated to deliver between at least 0.1 oz, at least 0.5 oz, at least 1 oz, at least 2 oz, or at least 4 oz, or at least 8 oz of nickel per acre. In certain embodiments, such formulations deliver ascaroside(s) in combination with any two or more of zinc, iron, manganese, boron, silicon, molybdenum, copper and nickel at any combination of the rates described above.

[0144] The formulations or compositions can be formulated as is conventional in the art and may be liquid or dry compositions. Dry compositions include powders and the like. The compositions can be utilized as liquid concentrates, Ready-To-Use (RTU) liquid sprays, dusts, or solids, depending upon the needs of the user. The formulation chosen will depend on the use of the product. In use, the composition can be applied directly to the plant.

[0145] In general, a formulation will include at least one ascaroside as described herein, or at least one ascaroside and one or more plant nutrients, and one or more agriculturally acceptable adjuvants (also referred to herein as “agriculturally suitable adjuvants”). Agriculturally suitable adjuvants are used to enhance the effectiveness of the compounds described herein and include, but are not limited to, surfactants, emulsifiers, oils, salts, and the like. The adjuvants may be added into the formulation or alternatively can be added separately at the time of application to 41 409753-015WO (210651) BUSINESS.31699770.1 the crops. In some embodiments, wetting agents, emulsifiers, spreaders, and the like may be used in the formulations. Formulations include concentrated versions, in which the present active agent (a compound as described herein) is present in a concentration of from 0.001 to 98.0 percent, with the remaining content being physiologically acceptable carriers. Such formulations, especially those with less than 50 percent of the present compound, can sometimes be used directly, but these formulations can also be diluted with other physiologically acceptable carriers to form more dilute treating formulations. These latter formulations can include the compounds described herein in lesser concentrations of from 0.001 to 0.1 percent.

[0146] The formulations may additionally contain “adjuvant surfactants” to enhance deposition, wetting, and penetration of the compounds onto the target crop and organism. These “adjuvant surfactants” may optionally be employed as a component of the formulation or as a tank mix. The amount of adjuvant surfactant will typically vary from 0.01 to 1.0 percent by volume, based on a spray-volume of water, preferably 0.05 to 0.5 volume percent. Suitable adjuvant surfactants include, but are not limited to ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulfosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines, blends of surfactants with mineral or vegetable oils, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9- Cu alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12- C16) ethoxylate; di -sec-butylphenol EO-PO block copolymer; polysiloxane-methyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99. The formulations may also include oil-in-water emulsions.

[0147] In the case of wettable powder formulations, “Surfactants” comprise typically about 0.5% to about 10% of the wettable powder. Suitable “Surfactants” for wettable powders include sulfonated lignins, condensed naphthalene-sulfonates, the naphthalene-sulfonates, alkyl- benenesulfonates, alkysulfonates or nonionic surfactants such as ethylene oxide adducts of alkylphenols or mixtures thereof.

[0148] Representative organic solvents which may be employed in preparing emulsifiable concentrates of the disclosed ascaroside(s) and / or plant nutrient(s) are the aromatic liquids such 42 409753-015WO (210651) BUSINESS.31699770.1 as xylene, propyl benzene fractions; or mixed naphthalene fractions, mineral oils, substituted aromatic organic liquids such as dioctyl phthalate; kerosene; dialkyl amides of various fatty acids, particularly the dimethyl amides of fatty glycols and glycol derivatives such as the n-butyl ether, ethyl ether or methyl ether of diethylene glycol, the methyl ether of triethylene glycol, amides of simple carboxylic acids, such as dimethyl formamide and dimethyl acetamide, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; terpenic solvents, rosin derivatives, aliphatic ketones such as cyclohexanone, complex aliphatic and aromatic alcohols such as 2-ethoxyethanol, vegetable oils such as soy bean oil, rape seed oil, olive oil, castor oil, sunflower seed oil, coconut oil, com oil, cotton seed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; and the like. Mixtures of two or more organic liquids may also be employed in the preparation of the emulsifiable concentrate. Organic liquids include xylene, and propyl benzene fractions, with xylene being most preferred in some cases. Surface-active dispersing agents are typically employed in liquid formulations and in an amount of from 0.1 to 20 percent by weight based on the combined weight of the dispersing agent with one or more of the compounds.

[0149] “Emulsifiers” for emulsifiable concentrates are typically mixed ionic and / or nonionic surfactants such as those mentioned herein or their equivalents. Examples of nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene. Cationic emulsifiers include quaternary ammonium compounds and fatty amine salts. Anionic emulsifiers include the oil soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil-soluble salts or sulfated polyglycol ethers and appropriate salts of phosphated- polyglycol ether.

[0150] Dusts containing the ascaroside(s) and / or plant nutrient(s) may be prepared by intimately mixing one or more of the compounds in powdered form with a suitable dusty agricultural carrier, such as, for example, kaolin clay, ground volcanic rock, and the like. Dusts can suitably contain from about 1 to about 10 weight percent of the compounds, based on the total weight of the dust. 43 409753-015WO (210651) BUSINESS.31699770.1

[0151] Wettable powders may be agglomerated or compacted to form water dispersible granules. These granules include mixtures of compounds, inert carriers suitable for granular applications, and surfactants. The concentration of the compound is typically between about 0.1% to about 90% by weight. The “inert carrier suitable for granular applications” is typically prophyllite, talc, chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein, gluten, montmorillonite clays, diatomaceous earths, purified silicates, or the like. In such operations, the finely divided carrier and surfactants are typically blended with the compound(s) and milled.

[0152] “Aqueous suspensions” may be prepared where the one or more ascarosides and / or one or more plant nutrients are dispersed in an aqueous vehicle at a concentration typically in the range of between about 5% to about 50% by weight. The suspensions are prepared by finely grinding the compound and vigorously mixing it into a vehicle of water, surfactants, and dispersants. Inert ingredients such as inorganic salts and synthetic or natural gums may also be employed to increase the density and / or viscosity of the aqueous vehicle as is desired. DEFINITIONS

[0153] In order for the present disclosure to be more readily understood, certain terms are defined below. Additional definitions for the following terms and other terms are set forth throughout the specification. In this application, unless otherwise clear from context, the term “a” may be understood to mean “at least one.”

[0154] As used in this application, the term “or” may be understood to mean “and / or.” In this application, the terms “comprising” and “including” may be understood to encompass itemized components or steps whether presented by themselves or together with one or more additional components or steps. As used in this application, the term “comprise” and variations of the term, such as “comprising” and “comprises,” are not intended to exclude other additives, components, integers or steps.

[0155] About, Approximately: As used herein, the terms “about” and “approximately” are used as equivalents. Unless otherwise stated, the terms “about” and “approximately” may be understood to permit standard variation as would be understood by those of ordinary skill in the art. Where ranges are provided herein, the endpoints are included. Any numerals used in this application with or without about / approximately are meant to cover any normal fluctuations appreciated by one of ordinary skill in the relevant art. Unless otherwise stated, the term above 44 409753-015WO (210651) BUSINESS.31699770.1 refers to within 25% of a given value. In some embodiments, the term “approximately” or “about” refers to a range of values that fall within 20 %, 19 %, 18 %, 17 %, 16 %, 15 %, 14 %, 13 %, 12 %, 11 %, 10 %, 9 %, 8 %, 7 %, 6 %, 5 %, 4 %, 3 %, 2 %, 1 %, or less in either direction (greater than or less than) of the stated reference value unless otherwise stated or otherwise evident from the context (except where such number would exceed 100 % of a possible value).

[0156] Definitions of specific functional groups and chemical terms are described in more detail below. For purposes of this invention, the chemical elements are identified in accordance with the Periodic Table of the Elements, CAS version, Handbook of Chemistry and Physics, 75th Ed., inside cover, and specific functional groups are generally defined as described therein. Additionally, general principles of organic chemistry, as well as specific functional moieties and reactivity, are described in Organic Chemistry, Thomas Sorrell, University Science Books, Sausalito, 1999; Smith and March March’s Advanced Organic Chemistry, 5th Edition, John Wiley & Sons, Inc., New York, 2001; Larock, Comprehensive Organic Transformations, VCH Publishers, Inc., New York, 1989; Carruthers, Some Modern Methods of Organic Synthesis, 3rd Edition, Cambridge University Press, Cambridge, 1987; the entire contents of each of which are incorporated herein by reference.

[0157] Certain compounds provided herein can comprise one or more asymmetric centers, and thus can exist in various stereoisomeric forms, e.g., enantiomers and / or diastereomers. Thus, inventive compounds and compositions thereof may be in the form of an individual enantiomer, diastereomer or geometric isomer, or may be in the form of a mixture of stereoisomers. In certain embodiments, compounds described herein are enantiopure compounds. In certain other embodiments, mixtures of enantiomers or diastereomers are provided.

[0158] Furthermore, certain compounds as described herein may have one or more double bonds that can exist as either a Z or E isomer, unless otherwise indicated. The compounds can be provided as individual isomers substantially free of other isomers and alternatively, as mixtures of various isomers, e.g., racemic mixtures of enantiomers.

[0159] As used herein, the term “isomers” includes any and all geometric isomers and stereoisomers. For example, “isomers” include cis– and trans–isomers, E– and Z– isomers, R– and S–enantiomers, diastereomers, (D)–isomers, (L)–isomers, racemic mixtures thereof, and 45 409753-015WO (210651) BUSINESS.31699770.1 other mixtures thereof, as falling within the scope of the disclosure. For instance, a compound may, in some embodiments, be provided substantially free of one or more corresponding stereoisomers, and may also be referred to as “stereochemically enriched.”

[0160] Where a particular enantiomer is preferred, it may, in some embodiments be provided substantially free of the opposite enantiomer, and may also be referred to as “optically enriched.” “Optically enriched,” as used herein, means that the compound is made up of a significantly greater proportion of one enantiomer. In certain embodiments the compound is made up of at least about 90% by weight of an enantiomer. In some embodiments the compound is made up of at least about 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9% by weight of an enantiomer. In some embodiments the enantiomeric excess of provided compounds is at least about 90%, 95%, 97%, 98%, 99%, 99.5%, 99.7%, 99.8%, or 99.9%. In some embodiments, enantiomers may be isolated from racemic mixtures by any method known to those skilled in the art, including chiral high pressure liquid chromatography (HPLC) and the formation and crystallization of chiral salts or prepared by asymmetric syntheses. See, for example, Jacques, et al., Enantiomers, Racemates and Resolutions (Wiley Interscience, New York, 1981); Wilen, S.H., et al., Tetrahedron 33:2725 (1977); Eliel, E.L. Stereochemistry of Carbon Compounds (McGraw–Hill, NY, 1962); Wilen, S.H. Tables of Resolving Agents and Optical Resolutions p. 268 (E.L. Eliel, Ed., Univ. of Notre Dame Press, Notre Dame, IN 1972).

[0161] The terms “halo” and “halogen” as used herein refer to an atom selected from fluorine (fluoro, –F), chlorine (chloro, –Cl), bromine (bromo, –Br), and iodine (iodo, –I).

[0162] The term “aliphatic” or “aliphatic group”, as used herein, denotes a hydrocarbon moiety that may be straight–chain (i.e., unbranched), branched, or cyclic (including fused, bridging, and spiro–fused polycyclic) and may be completely saturated or may contain one or more units of unsaturation, but which is not aromatic. Unless otherwise specified, aliphatic groups contain 1– 30 carbon atoms. In certain embodiments, aliphatic groups contain 1–12 carbon atoms. In certain embodiments, aliphatic groups contain 1–8 carbon atoms. In certain embodiments, aliphatic groups contain 1–6 carbon atoms. In some embodiments, aliphatic groups contain 1–5 carbon atoms, in some embodiments, aliphatic groups contain 1–4 carbon atoms, in yet other embodiments aliphatic groups contain 1–3 carbon atoms, and in yet other embodiments aliphatic groups contain 1–2 carbon atoms. Suitable aliphatic groups include, but are not limited to, linear 46 409753-015WO (210651) BUSINESS.31699770.1 or branched, alkyl, alkenyl, and alkynyl groups, and hybrids thereof such as (cycloalkyl)alkyl, (cycloalkenyl)alkyl or (cycloalkyl)alkenyl.

[0163] The term “heteroaliphatic” or “heteroaliphatic group”, as used herein, denotes an aliphatic group where one or more carbon or hydrogen atoms are replaced by a heteroatom (e.g. oxygen, nitrogen, sulfur, phosphorous, boron, etc.). In some embodiments, a heteroaliphatic group is a heterocyclyl group.

[0164] The term "unsaturated", as used herein, means that a moiety has one or more double or triple bonds.

[0165] The term “alkyl,” as used herein, refers to saturated, straight– or branched–chain hydrocarbon radicals derived from an aliphatic moiety containing between one and six carbon atoms by removal of a single hydrogen atom. Unless otherwise specified, alkyl groups contain 1–12 carbon atoms. In certain embodiments, alkyl groups contain 1–8 carbon atoms. In certain embodiments, alkyl groups contain 1–6 carbon atoms. In some embodiments, alkyl groups contain 1–5 carbon atoms, in some embodiments, alkyl groups contain 1–4 carbon atoms, in yet other embodiments alkyl groups contain 1–3 carbon atoms, and in yet other embodiments alkyl groups contain 1–2 carbon atoms. Examples of alkyl radicals include, but are not limited to, methyl, ethyl, n–propyl, isopropyl, n–butyl, iso–butyl, sec–butyl, sec–pentyl, iso–pentyl, tert– butyl, n–pentyl, neopentyl, n–hexyl, sec–hexyl, n–heptyl, n–octyl, n–decyl, n–undecyl, dodecyl, and the like.

[0166] The term “alkenyl,” as used herein, denotes a monovalent group derived from a straight– or branched–chain aliphatic moiety having at least one carbon–carbon double bond by the removal of a single hydrogen atom. Unless otherwise specified, alkenyl groups contain 2–12 carbon atoms. In certain embodiments, alkenyl groups contain 2–8 carbon atoms. In certain embodiments, alkenyl groups contain 2–6 carbon atoms. In some embodiments, alkenyl groups contain 2–5 carbon atoms, in some embodiments, alkenyl groups contain 2–4 carbon atoms, in yet other embodiments alkenyl groups contain 2–3 carbon atoms, and in yet other embodiments alkenyl groups contain 2 carbon atoms. Alkenyl groups include, for example, ethenyl, propenyl, butenyl, 1–methyl–2–buten–1–yl, and the like.

[0167] The term “aryl” used alone or as part of a larger moiety as in “aralkyl”, “aralkoxy”, or “aryloxyalkyl”, refers to monocyclic and polycyclic ring systems having a total of five to 20 ring 47 409753-015WO (210651) BUSINESS.31699770.1 members, wherein at least one ring in the system is aromatic and wherein each ring in the system contains three to twelve ring members. The term “aryl” may be used interchangeably with the term “aryl ring”. In certain embodiments, “aryl” refers to an aromatic ring system which includes, but is not limited to, phenyl, biphenyl, naphthyl, anthracyl and the like, which may bear one or more substituents. Also included within the scope of the term “aryl”, as it is used herein, is a group in which an aromatic ring is fused to one or more additional rings, such as benzofuranyl, indanyl, phthalimidyl, naphthimidyl, phenantriidinyl, or tetrahydronaphthyl, and the like.

[0168] The terms “heteroaryl” and “heteroar–,” used alone or as part of a larger moiety, e.g., “heteroaralkyl,” or “heteroaralkoxy,” refer to groups having 5 to 10 ring atoms, preferably 5, 6, or 9 ring atoms; having 6, 10, or 14 ^ ^electrons shared in a cyclic array; and having, in addition to carbon atoms, from one to five heteroatoms. The term “heteroatom” refers to nitrogen, oxygen, or sulfur, and includes any oxidized form of nitrogen or sulfur, and any quaternized form of a basic nitrogen. Heteroaryl groups include, without limitation, thienyl, furanyl, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, indolizinyl, purinyl, naphthyridinyl, and pteridinyl. The terms “heteroaryl” and “heteroar–”, as used herein, also include groups in which a heteroaromatic ring is fused to one or more aryl, cycloaliphatic, or heterocyclyl rings, where the radical or point of attachment is on the heteroaromatic ring. Nonlimiting examples include indolyl, isoindolyl, benzothienyl, benzofuranyl, dibenzofuranyl, indazolyl, benzimidazolyl, benzthiazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 4H–quinolizinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, and pyrido[2,3–b]–1,4–oxazin– 3(4H)–one. A heteroaryl group may be monocyclic, bicyclic, bridged bicyclic, or spirocyclic. The term “heteroaryl” may be used interchangeably with the terms “heteroaryl ring,” “heteroaryl group,” or “heteroaromatic,” any of which terms include rings that are optionally substituted. The term “heteroaralkyl” refers to an alkyl group substituted by a heteroaryl, wherein the alkyl and heteroaryl portions independently are optionally substituted. The term “heteroarylenyl” refers to bivalent heteroaryl groups (e.g., pyridylenyl). 48 409753-015WO (210651) BUSINESS.31699770.1

[0169] As used herein, the terms “heterocycle,” “heterocyclyl,” “heterocyclic radical,” and “heterocyclic ring” are used interchangeably and refer to a stable 5– to 7–membered monocyclic or 7–10–membered bicyclic heterocyclic moiety that is either saturated or partially unsaturated, and having, in addition to carbon atoms, one or more, preferably one to four, heteroatoms, as defined above. When used in reference to a ring atom of a heterocycle, the term "nitrogen" includes a substituted nitrogen. As an example, in a saturated or partially unsaturated ring having 0–3 heteroatoms selected from oxygen, sulfur or nitrogen, the nitrogen may be N (as in 3,4– dihydro–2H–pyrrolyl), NH (as in pyrrolidinyl), or +NR (as in N–substituted pyrrolidinyl).

[0170] A heterocyclic ring can be attached to its pendant group at any heteroatom or carbon atom that results in a stable structure and any of the ring atoms can be optionally substituted. Examples of such saturated or partially unsaturated heterocyclic radicals include, without limitation, tetrahydrofuranyl, tetrahydrothiophenyl pyrrolidinyl, piperidinyl, pyrrolinyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl, oxazolidinyl, piperazinyl, dioxanyl, dioxolanyl, diazepinyl, oxazepinyl, thiazepinyl, morpholinyl, and quinuclidinyl. The terms “heterocycle,” “heterocyclyl,” “heterocyclyl ring,” “heterocyclic group,” “heterocyclic moiety,” and “heterocyclic radical,” are used interchangeably herein, and also include groups in which a heterocyclyl ring is fused to one or more aryl, heteroaryl, or cycloaliphatic rings, such as indolinyl, 3H–indolyl, chromanyl, phenanthridinyl, or tetrahydroquinolinyl. In some embodiments, a heterocyclic ring may be a 5-12 membered bicyclic, bridged bicyclic, or spirocyclic ring. A heterocyclic ring may include one or more oxo (=O) or thioxo (=S) substituent. The term “heterocyclylalkyl” refers to an alkyl group substituted by a heterocyclyl, wherein the alkyl and heterocyclyl portions independently are optionally substituted.

[0171] As used herein, the term “partially unsaturated” refers to a ring moiety that includes at least one double or triple bond. The term “partially unsaturated” is intended to encompass rings having multiple sites of unsaturation, but is not intended to include aryl or heteroaryl moieties, as herein defined.

[0172] As described herein, compounds as provided herein may contain “optionally substituted” moieties. In general, the term “substituted”, whether preceded by the term “optionally” or not, means that one or more hydrogens of the designated moiety are replaced with a suitable substituent. Unless otherwise indicated, an “optionally substituted” group may have a suitable 49 409753-015WO (210651) BUSINESS.31699770.1 substituent at each substitutable position of the group, and when more than one position in any given structure may be substituted with more than one substituent selected from a specified group, the substituent may be either the same or different at every position. Combinations of substituents envisioned are preferably those that result in the formation of stable or chemically feasible compounds. The term “stable,” as used herein, refers to compounds that are not substantially altered when subjected to conditions to allow for their production, detection, and, in certain embodiments, their recovery, purification, and use for one or more of the purposes disclosed herein.

[0173] Suitable monovalent substituents on a substitutable carbon atom of an “optionally substituted” group are independently halogen; –(CH2)0–4R ^; –(CH2)0–4OR ^; -O-(CH2)0-4C(O)OR°; –(CH2)0–4CH(OR ^)2; –(CH2)0–4SR ^; –(CH2)0–4Ph, which may be substituted with R°; –(CH2)0–4O(CH2)0–1Ph which may be substituted with R°; –CH=CHPh, which may be substituted with R°; –NO2; –CN; –N3; –(CH2)0–4N(R ^)2; –(CH2)0–4N(R ^)C(O)R ^; –N(R ^)C(S)R ^; –(CH2)0-4N(R ^)C(O)NR ^2; –N(R ^)C(S)NR ^2; –(CH2)0–4N(R ^)C(O)OR ^; -N(R ^)N(R ^)C(O)R ^; –N(R ^)N(R ^)C(O)NR ^2; –N(R ^)N(R ^)C(O)OR ^; –(CH2)0–4C(O)R ^; -C(S)R ^; –(CH2)0–4C(O)OR ^; –(CH2)0–4C(O)N(R ^)2; –(CH2)0–4C(O)SR ^; –(CH2)0–4C(O)OSiR ^3; –(CH2)0–4OC(O)R ^; –OC(O)(CH2)0–4SR–, SC(S)SR°; –(CH2)0–4SC(O)R ^; –(CH2)0–4C(O)NR ^2; -C(S)NR ^2; –C(S)SR°; –SC(S)SR°, –(CH2)0–4OC(O)NR ^2; –C(O)N(OR ^)R ^; –C(O)C(O)R ^; -C(O)CH2C(O)R ^; –C(NOR ^)R ^; –(CH2)0–4SSR ^; –(CH2)0–4S(O)2R ^; –(CH2)0–4S(O)2OR ^; -(CH2)0–4OS(O)2R ^; –S(O)2NR ^2; –(CH2)0–4S(O)R ^; –N(R ^)S(O)2NR ^2; –N(R ^)S(O)2R ^; -N(OR ^)R ^; –C(NH)NR ^2; –P(O)2R ^; –P(O)R ^2; –OP(O)R ^2; –OP(O)(OR ^)2; SiR ^3; –(C1–4 straight or branched alkylene)O–N(R ^)2; or –(C1–4 straight or branched alkylene)C(O)O–N(R ^)2, wherein each R ^ may be substituted as defined below and is independently hydrogen, C1-8 aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the definition above, two independent occurrences of R ^, taken together with their intervening atom(s), form a 3–12–membered saturated, partially unsaturated, or aryl mono– or polycyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, which may be substituted as defined below. 50 409753-015WO (210651) BUSINESS.31699770.1

[0174] Suitable monovalent substituents of R ^ together with their intervening atoms), are independently halogen, –(CH2)0–2R^, –(haloR^), –(CH2)0–2OH, –(CH2)0–2OR^, –(CH2)0–2CH(OR^)2; -O(haloR^), –CN, –N3, –(CH2)0–2C(O)R^, –(CH2)0–2C(O)OH, –(CH2)0–2C(O)OR^, -(CH2)0-4C(O)N(R ^)2; –(CH2)0–2SR^, –(CH2)0–2SH, –(CH2)0–2NH2, –(CH2)0–2NHR^, -(CH2)0-2NR^2, –NO2, –SiR^3, –OSiR^3, –C(O)SR^, –(C1–4 straight or branched alkylene)C(O)OR^, or –SSR^wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently selected from C1–4 aliphatic, -CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents on a saturated carbon atom of R ^ include =O and =S.

[0175] Suitable divalent substituents on a saturated carbon atom of an “optionally substituted” group include the following: =O, =S, =NNR*2, =NNHC(O)R*, =NNHC(O)OR*, =NNHS(O)2R*, =NR*, =NOR*, –O(C(R*2))2–3O–, or –S(C(R*2))2–3S–, wherein each independent occurrence of R*is selected may be substituted as defined below, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur. Suitable divalent substituents that are bound to vicinal substitutable carbons of an “optionally substituted” group include: –O(CR*2)2–3O–, wherein each independent occurrence of R*is selected from hydrogen, C1–6 aliphatic which may be substituted as defined below, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0176] Suitable substituents on the aliphatic group of R*include halogen, –R^, -(haloR^), –OH, –OR^, –O(haloR^), –CN, –C(O)OH, –C(O)OR^, –NH2, –NHR^, –NR^2, or –NO2, wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4 aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0177] Suitable substituents on a substitutable nitrogen of an “optionally substituted” group include –R†, –NR†2, –C(O)R†, –C(O)OR†, –C(O)C(O)R†, –C(O)CH2C(O)R†, –S(O)2R†, -S(O)2NR†2, –C(S)NR†2, –C(NH)NR†2, or –N(R†)S(O)2R†; wherein each R†is independently 409753-015WO (210651) hydrogen, C1–6aliphatic which may be substituted as defined below, unsubstituted –OPh, or an unsubstituted 5–6–membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur, or, notwithstanding the definition above, two independent occurrences of R†, taken together with their intervening atom(s) form an unsubstituted 3–12–membered saturated, partially unsaturated, or aryl mono– or bicyclic ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0178] Suitable substituents on the aliphatic group of R†are independently halogen, –R^, – (haloR^), –OH, –OR^, –O(haloR^), –CN, –C(O)OH, –C(O)OR^, –NH2, –NHR^, –NR^2, or -NO2, wherein each R^is unsubstituted or where preceded by “halo” is substituted only with one or more halogens, and is independently C1–4aliphatic, –CH2Ph, –O(CH2)0–1Ph, or a 5-6-membered saturated, partially unsaturated, or aryl ring having 0–4 heteroatoms independently selected from nitrogen, oxygen, or sulfur.

[0179] As used herein, the term “substantially” refers to the qualitative condition of exhibiting total or near-total extent or degree of a characteristic or property of interest.

[0180] The convention of naming ascarosides by a several-letter prefix followed by a pound sign (#) and a number is sometimes used (for example ascr#18). This convention is used in the scientific literature and the skilled artisan will understand that each such name is associated with a specific chemical structure of known composition and will readily apprehend the structure of the molecule referred to using this naming convention. Unless otherwise indicated, all compound identifiers of this format used herein conform to the definitions described in the C. elegans Small Molecule Identifier Database (SMID-DB) maintained on the World Wide Web at smid-db.org. EXAMPLES Example 1: Ascaroside zinc micronutrient trial in Soybeans

[0181] A trial was performed to evaluate the effect of foliar application of the ascaroside oscr#16 in combination with zinc. The trial was performed in a 10 acre commercial soybean field in the Eastern US, divided into two areas of approximately 5 acres each. The crop was planted and maintained using typical practices for the region, at approximately the growth stages of V5 and R2 / R3, half of the field was treated with a foliar spray including 4 oz / acre of a composition containing 0.04 wt% of the ascaroside oscr#16 and 4.0 wt% soluble zinc (as zinc sulfate) which 52 409753-015WO (210651) BUSINESS.31699770.1 was diluted in sufficient water to enable good crop coverage (corresponding to application of approximately 50 mg of ascaroside and 0.2 oz of zinc per acre).

[0182] The field was observed periodically to assess differences in plant health and vigor in the treated vs untreated areas. The treated and untreated areas were harvested separately once the crop reached maturity. The plot treated with the ascaroside zinc composition was visibly healthier during the growing season and the soybean plants in the treated area retained their foliage later into the growing season than plants in the untreated area. Upon harvest, the treated area produced a yield of 58.8 Bu / ac treated vs. 48.5 Bu / ac for the untreated field, corresponding to a 21% yield improvement from application of the inventive ascaroside composition. Example 2: Ascaroside / multinutrient trial in soybean

[0183] A trial is performed according to the protocol of Example 1, except the applied composition is used at 20 oz per acre and contains 0.003% oscr#16 in combination with a muti- nutrient composition (Awaken® from Loveland Agri Products) which contains 20% nitrogen, 21% potassium, 0.02% boron, 0.19% copper, 0.19% iron, 0.19% manganese, 0.0007% molybdenum, and 3.36% zinc. Example 3: Ascaroside / boron trial in soybean

[0184] A trial is performed according to the protocol of Example 1, except the applied composition contains 0.005% oscr#16 in combination with a composition which contains 2% boron applied at a rate of 32 oz per acre. Example 4: Ascaroside / zinc trial in soybean

[0185] A trial is performed according to the protocol of Example 1, except the applied composition contains the ascaroside ascr#18 instead of oscr#16. Examples 5,6,7: Ascaroside nutrient trials in Corn

[0186] Trials are performed according to the protocols of Examples 1-4, except the compositions are applied to corn instead of soybeans. Examples 8,9,10: Ascaroside nutrient trials in Rice 53 409753-015WO (210651) BUSINESS.31699770.1

[0187] Trials are performed according to the protocols of Examples 1-4, except the compositions are applied to rice instead of soybeans and the amount of ascaroside in each composition is reduced to 1 / 10 of the amounts of Examples 1-4. Examples 11,12,13: Ascaroside nutrient trials in wheat

[0188] Trials are performed according to the protocols of Examples 1-4, except the compositions are applied to wheat instead of soybeans. Example 14: The trials above are repeated, but the identity of the ascaroside is changed to evaluate the activity of other ascarosides relative to oscr#16 and ascr#18.

[0189] It is contemplated that compounds, compositions, and methods of the present application encompass variations and adaptations developed using information from the embodiments described in the present disclosure. Adaptation or modification of the methods and processes described in this specification may be performed by those of ordinary skill in the relevant art.

[0190] It will be appreciated that use of headers in the present disclosure are provided for the convenience of the reader. The presence and / or placement of a header is not intended to limit the scope of the subject matter described herein. Unless otherwise specified, embodiments located in one section of the application apply throughout the application to other embodiments, both singly and in combination.

[0191] Throughout the description, where compositions, compounds, or products are described as having, including, or comprising specific components, or where processes and methods are described as having, including, or comprising specific steps, it is contemplated that, additionally, there are articles, devices, and systems of the present application that consist essentially of, or consist of, the recited components, and that there are processes and methods according to the present application that consist essentially of, or consist of, the recited processing steps.

[0192] It should be understood that the order of steps or order for performing certain action is immaterial so long as the described method remains operable. Moreover, two or more steps or actions may be conducted simultaneously.

[0193] All publications and patent applications mentioned in the specification are indicative of the level of those skilled in the art to which this invention pertains. All publications and patent applications are herein incorporated by reference to the same extent as if each individual 54 409753-015WO (210651) BUSINESS.31699770.1 publication or patent application was specifically and individually indicated to be incorporated by reference.

[0194] Although the foregoing invention has been described in some detail by way of illustration and example for purposes of clarity of understanding, it will be obvious that certain changes and modifications may be practiced within the scope of the appended claims. 55 409753-015WO (210651) BUSINESS.31699770.1

Claims

CLAIMS What is claimed is:

1. A method for providing nutrients and protection against pathogens to a plant, comprising contacting a plant, a plant part, or soil surrounding a plant with an effective amount of a combination of agents, said agents comprising one or more ascaroside and one or more plant nutrients.

2. A method for providing nutrients and protection against pathogens to a plant, the method comprising administering an ascaroside to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received nutrients (e.g., via administration to the plant, plant part, or soil surrounding the plant or plant part).

3. A method for providing nutrients and protection against pathogens to a plant, the method comprising administering nutrients to a plant, plant part, or soil surrounding the plant or plant part, wherein the plant, plant part, or soil surrounding the plant or plant part is receiving or has received an ascaroside (e.g., via administration to the plant, plant part, or soil surrounding the plant or plant part).

4. The method of claim 1, wherein the one or more plant nutrients comprise one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

5. The method of claim 1, wherein the one or more plant nutrients comprise one or more micronutrients selected from the group consisting of boron-containing nutrients, chlorine- containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese- containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof. 56 409753-015WO (210651) BUSINESS.31699770.

16. The method of claim 1, wherein the one or more plant nutrients comprise one or more macronutrients and one or more micronutrients.

7. The method of any one of claims 1-6, wherein the one or more ascarosides comprises an ascaroside having the structure (I): OZ where:Z is an optionally substituted C3-40aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20 aliphatic, C1-20 acyl, C1-20 heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20carbonate (e.g. -a moiety -C(O)ORc), a C2-20 carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20 thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from - H, optionally substituted C1-12aliphatic, optionally substituted C1-12heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

8. The method of claim 7, wherein Z is selected from the group consisting of: (i) –CH(CH3)–R1, where R1is an optionally substituted C1-40 aliphatic group; 57 409753-015WO (210651) BUSINESS.31699770.1(ii) –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (iii) –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (iv) –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (v) –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (vi) –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (vii) –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (viii) –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and (ix) –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

9. The method of claim 7, wherein Z is selected from the group consisting of: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, 58 409753-015WO (210651) BUSINESS.31699770.1an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a 59 409753-015WO (210651) BUSINESS.31699770.1peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and (xix) an optionally unsaturated, optionally substituted C2-40 sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

10. The method of any one of claims 1-9, wherein one or more ascarosides comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.

11. The method of any one of claims 1-9, wherein the one or more ascarosides comprises ascr#18.

12. The method of any one of claims 1-11, wherein the one or more ascarosides and the one or more plant nutrients are applied simultaneously.

13. The method of claim 12, wherein the one or more ascarosides and the one or more plant nutrients are contained within the same composition. 60 409753-015WO (210651) BUSINESS.31699770.

114. The method of any one of claims 1-13, wherein the one or more ascarosides and the one or more plant nutrients are applied sequentially.

15. The method of any one of claims 1-14, wherein the combination is used as a seed coating.

16. A composition comprising one or more ascarosides and one or more plant nutrients.

17. The composition of claim 16, wherein the one or more ascarosides and the one or more plant nutrients are present in effective amounts.

18. The composition of claim 16 or 17, wherein the one or more plant nutrients comprise one or more macronutrients selected from the group consisting of nitrogen-containing nutrients, phosphorus-containing nutrients, potassium-containing nutrients, calcium-containing nutrients, magnesium-containing nutrients, sulfur-containing nutrients, and combinations thereof.

19. The composition of claim 16 or 17, wherein the one or more plant nutrients comprise one or more micronutrients selected from the group consisting of boron-containing nutrients, chlorine-containing nutrients, copper-containing nutrients, iron-containing nutrients, manganese-containing nutrients, molybdenum-containing nutrients, zinc-containing nutrients, and combinations thereof.

20. The composition of claim 16 or 17, wherein the one or more plant nutrients comprise one or more macronutrients and one or more micronutrients.

21. The composition of any one of claims 16-20 wherein the one or more ascarosides comprises an ascaroside having the structure (I): OZ 409753-015WO (210651) BUSINESS.31699770.1where: Z is an optionally substituted C3-40 aliphatic group, and each of Raand Rbis independently -H, or an optionally substituted moiety selected from the group consisting of: C1-20aliphatic, C1-20acyl, C1-20heteroaliphatic, aryl, heteroaryl, a hydroxyl protecting group, a phosphorous-linked functional group , a sulfur-linked functional group, a silicon-linked functional group, a C2-20 carbonate (e.g. -a moiety -C(O)ORc), a C2-20carbamate (e.g. -a moiety -C(O)N(Rc)2), a C2-20thioester (e.g. a moiety -C(S)Rc), a C2-20 thiocarbonate (e.g. a moiety -C(S)ORc), a C2-20 dithiocarbonate (e.g. a moiety -C(S)SRc), a C1-20 thiocarbamate (e.g. a moiety -C(S)N(Rc)2), a sugar moiety, a peptide, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule. Where Rcis independently at each occurrence selected from - H, optionally substituted C1-12 aliphatic, optionally substituted C1-12 heteroaliphatic, optionally substituted aryl, optionally substituted heteroaryl, a polymer chain, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule, and where Raand Rbmay be taken together to form an optionally substituted ring, optionally containing one or more heteroatoms, and optionally containing one or more sites of unsaturation.

22. The composition of claim 21, wherein Z is selected from the group consisting of: (i) –CH(CH3)–R1, where R1is an optionally substituted C1-40aliphatic group; (ii) –CH(CH3)–(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (iii) –CH(CH3)–(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (iv) –CH(CH3)–(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; 62 409753-015WO (210651) BUSINESS.31699770.1(v) –CH(CH3)–(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (vi) –(CH2)n–CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (vii) –(CH2)n–CH=CH-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; (viii) –(CH2)n–CH(OH)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide; and (ix) –(CH2)n–C(O)–CH2-CO2R2, where n is an integer from 1 to 40, and R2is -H, a metal cation, an optionally substituted C1-20 aliphatic group, an optionally substituted aromatic group, a glycoside, an amino acid, a peptide, or a nucleotide.

23. The composition of claim 21, wherein Z is selected from the group consisting of: (x) –CH(CH3)–(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xi) –CH(CH3)–(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; 63 409753-015WO (210651) BUSINESS.31699770.1(xii) –CH(CH3)–(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiii) –CH(CH3)–(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xiv) –(CH2)n–CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xv) –(CH2)n–CH=CH-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; (xvi) –(CH2)n–CH(OH)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; 64 409753-015WO (210651) BUSINESS.31699770.1(xvii) –(CH2)n–C(O)–CH2-CON(R3)2, where n is an integer from 1 to 40, and each R3is independently -H, an optionally substituted C1-20 aliphatic group, an optionally substituted C1-20 heteroaliphatic group, an optionally substituted aromatic group, an optionally substituted heteroaryl group, a polymer chain, an amino acid, a peptide, a nucleotide, or a linkage via a bond or a carbon-containing linker moiety to another ascaroside molecule; and (xvii) an optionally unsaturated, optionally substituted C2-40sidechain terminating in a chain end comprising a nitrogen-, oxygen- or sulfur-containing functional group.

24. The composition of any one of claims 16-23, wherein the one or more ascarosides comprises an ascaroside selected from the group consisting of ascr#9, ascr#10, ascr#16, ascr#18, ascr#20, ascr#22, and ascr#24.

25. The composition of any one of claims 16-23, wherein the one or more ascarosides comprises ascr#18.

26. The composition of any one of claims 16-25, wherein said composition is in a liquid form.

27. The composition of claim 26, wherein the liquid form is a sprayable formulation.

28. The composition of any one of claims 16-25, wherein the composition is in a solid form.

29. The composition of claim 28, wherein said solid form comprises powder or granules.

30. The composition of any one of claims 16-29, wherein the composition is stable for a period of greater than 6 months.

31. The composition of any one of claims 16-30, wherein the composition further comprises one or more additional components selected from the group consisting of surfactants, including emulsifiers, dispersants, foam-formers, colorants, processing aids, lubricants, fillers, reinforcements, flame retardants, light stabilizers, ultraviolet radiation absorbers, weather 65 409753-015WO (210651) BUSINESS.31699770.1stabilizers, plasticizers, release agents, perfumes, heat-retaining additives (e.g., silica), cross- linking agents, antioxidants, anti-foaming agents, buffers, pH modifiers, compatibility agents, drift control additives, extenders / stickers, tackifiers, plant penetrants, safeners, spreaders, and wetting agents. 66 409753-015WO (210651) BUSINESS.31699770.1

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